Can I trade my 2021 1st rd pick on draft day 2021, and then trade my 2022 1st rd pick on draft day 2022 a year later? Yes.

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Actually, the answers are NO, NO, and NO. You cannot trade future picks beyond 7 years. For the 2013/14 season, that means 2020 picks are the last ones eligible to be moved. In other words, while the Pistons are allowed to trade their ’20 first-rounder, they can’t part with their ’21 pick until July.

Can I trade my 2021 1st rd pick on draft day 2021, and then trade my 2022 1st rd pick on draft day 2022 a year later? Yes.

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A draft pick is considered a future pick until it has been taken. So yeah, sure, you can call up Johnny the GM on draft day an be like "Hey, Ill draft who you want plus toss in next years draft pick for player X". This action doesn't violate the Stepien rule. These are one of the exceptions.